Download BASIC NOMENCLATURE ABLE TO: 1.

BASIC NOMENCLATURE
A STUDENT WHO HAS MASTERED THE MATERIAL IN THIS SECTION SHOULD BE
ABLE TO:
1.
Give the IUPAC names of open-chain alkanes, alkenes (including cis and trans), alkynes,
alkyl halides, and alcohols having a longest chain of ten carbons or less when given the
structure, and draw the structure given the name. The unbranched alkanes whose names are
the basis of this are:
methane (1 carbon)
ethane (2 C’s)
propane (3 C’s)
butane (4 C’s)
pentane (5 C’s)
hexane (6 C’s)
heptane (7 C’s)
octane (8 C’s)
nonane (9 C’s)
decane (10 C’s)
The names of the groups you must be able to recognize and draw are:
methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl (the unbranched
groups)
isopropyl
isobutyl, sec-butyl, tert-butyl
neopentyl
vinyl and allyl
2.
Give the IUPAC name when given the structure, and give the structure given the IUPAC
name, of monocyclic alkanes, alkenes, alkynes, alcohols, and alkyl halides having rings
containing 3-10 carbons. These compounds may also contain halogen atoms and side
chains.
3.
Give the IUPAC name when given the structure, and draw the structure given the name, of
bicyclic alkanes. These alkanes may have alkyl groups or halogen atoms as substituents.
4.
Give the common name when given the structure, and give the structure when given the
common name, of simple alcohols and alkyl halides. In the system used here compounds
are named by first naming the alkyl group and then naming the functional group (e. g. ethyl
alcohol, neopentyl bromide).
5.
Give the common name when given the structure, and draw the structure when given the
common name, of unsubstituted monocyclic alcohols and alkyl halides (e. g. cyclobutyl
alcohol).
6.
Draw the structure when given any of the following common names: ethylene, propylene,
isobutylene, acetylene, and alkylacetylenes including any of the alkyl groups named in #1
above. Also, give the name when given the structure of any of these compounds.
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A STUDENT WHO HAS MASTERED THE OBJECTIVES ON THE PREVIOUS PAGE
SHOULD BE ABLE TO SOLVE THE FOLLOWING PROBLEMS AND RELATED ONES:
1.1
Give the IUPAC name of each of the compounds shown.
a) CH3 CH2 CH2 CH2 CH3
c) CH3 CH2 CHCH 3
|
OH
d) CH3 CH2 CHCH 2 CH3
|
CH3
e) (CH3 )2 CHCHBrCH 2 CH3
f) (C2 H5 )2 CH(CH 2 )2 CH3
g)
h) CH3 CBr2 CH2 CCl3
i) CH3 CH2 CHCH 2 CH2 CH3
|
CH2 OH
j) (CH3 )2 CHCH 2 CH2 C=CH 2
|
CH3
k)
l) CH3 CH2
C
Br
1.2
b) CHCl3
Br
CH3
CH3
|
|
CH3 CH2 CHCH 2 CHCHCH 3
|
CH2 CH2 CH3
CH3
|
CH3 CH2 C-C≡C-CH(CH 3 )2
|
CH3
m) CH3 CH2
C
C
H
CH3 CH2
H
C
H
Draw the structure of each of the compounds named below.
a) 2,2-dimethylbutane
b) 3,3-dimethyl-1-butanol
c) 4-ethyl-2,2-dimethylhexane
d) 1,2-dibromo-2-methylpropane
e) 4-methyl-2-pentyne
f) cis-1-bromo-2-pentene
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2.1
2.2
3.1
Give the IUPAC name of each of the compounds shown.
CH3
a)
b) (CH3 )2 CH
c)
OH
d) Cl
Draw the structure of each of the compounds named.
a) 1,3-dimethylcyclobutane b) 4-neopentylcyclohexanol
Cl
c) 4-isopropylcyclohexene
Give the name of each of the compounds shown.
CH3
a)
b)
c) Cl
d)
CH3
3.2
Draw the structure of each of these compounds.
a) bicyclo[2.2.0]hexane
b) 2-isopropylbicyclo[1.1.0]butane
c) 1,5-diethylbicyclo[3.3.0]octane
4.1
Give the common name of each of the compounds shown.
a) CH3 CH2 OH
b) CH3 CH2 CH2 Cl
c) (CH3 )3 C-CH2 OH
d) FC(CH3 )3
Draw the structure of each of the compounds named.
a) methyl iodide
b) isobutyl alcohol
c) isopropyl alcohol
d) sec-butyl bromide
4.2
5.1
Give the common name of each of the following compounds.
Br
OH
a)
b)
c)
OH
5.2
Draw the structures of the following compounds.
a) cyclopropyl chloride
b) cyclohexyl iodide
6.
Draw the structures of each of the following compounds.
a) propylene
b) acetylene
c) ethylacetylene
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d) ethylene
SOLUTIONS TO SAMPLE PROBLEMS:
1.1
a) pentane b) trichloromethane c) 2-butanol d) 3-methylpentane
e) 3-bromo-2-methylpentane f) 3-ethylhexane g) 5-isopropyl-3-methyloctane
h) 3,3-dibromo-1,1,1-trichlorobutane i) 2-ethyl-1-pentanol j) 2,5-dimethyl-1-hexene
k) 2,5,5-trimethyl-3-heptyne l) trans-1,2-dibromo-1-butene m) 2-ethyl-1-butene
1.2
a) 2,2-dimethylbutane
CH3
|
CH3 CCH2 CH3
|
CH3
b) 3,3-dimethyl-1-butanol
CH3
|
HOCH 2 CH2 CCH3
|
CH3
c) 4-ethyl-2,2-dimethylhexane
d) 1,2-dibromo-2-methylpropane
CH3 CH2 CH3
CH3
|
|
|
CH3 CCH2 CHCH 2 CH3
CH2 CCH3
|
|
|
CH3
Br Br
e) 4-methyl-2-pentyne
CH3 C≡CCHCH 3
|
CH3
f) cis-1-bromo-2-pentene
BrCH2
CH2 CH3
C
C
H
H
2.1
a) cycloheptane
c) 2-methylcyclobutanol
2.2
a) 1,3-dimethylcyclobutane b) 4-neopentylcyclohexanol c) 4-isopropylcyclohexene
CH3
|
CH3
CH3 HO
CH2 C-CH3
|
CH3
a) bicyclo[4.3.0]nonane
b) bicyclo[3.2.1]octane
c) 7-chlorobicyclo[4.1.1]octane
d) 1,6-dimethylbicyclo[3.2.0]heptane
3.1
3.2
b) isopropylcyclopentane
d) 1,4-dichlorocyclohexene
The structures are:
CH2 CH3
a)
b)
CH(CH 3 )2
c)
CH2 CH3
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4.1
a) ethyl alcohol b) propyl chloride c) neopentyl alcohol d) tert-butyl fluoride
4.2
a) methyl iodide
b) isobutyl alcohol
CH3 I
(CH3 )2 CHCH 2 OH
5.1
a) cyclopentyl alcohol
5.2
a) cyclopropyl chloride
a) propylene
CH3 CH=CH 2
(CH3 )2 CHOH
b) cyclohexyl alcohol
d) sec-butyl bromide
CH3 CHBrCH 2 CH3
c) cyclobutyl bromide
b) cyclohexyl iodide
Cl
6.
c) isopropyl alcohol
I
b) acetylene
H-C≡C-H
c) ethylacetylene
CH3 CH2 C≡C-H
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d) ethylene
H2 C=CH 2
Name ___________________________________________________ Third Drill Test (Sample)
Organic Chemistry 2210 DR
Answer All Questions
1) Name Cl3 CCH2 Cl
6) Draw neopentylcyclohexane
2) Name (CH3 )2 CH(CH 2 )3 CH(CH 3 )2
7) Draw 2,4-dibromo-3-ethylhexane
3) Name BrCHCH2 CH2 CHCH 2 CH3
|
|
CH2
CHOH
|
|
CH3
CH3
8) Draw 3,3-dimethylcyclobutanol
4) Name:
9) Name:
CH3
|
CHCH 2 CH3
CH3
CH3
5) Name
10) Draw cyclopentyl fluoride
OH
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11)Name
14)Give a structure for: propylacetylene
Br
12)Name:
15)Give a structure for:
4-methyl-1-neopentylbicyclo[3.2.1]octane
13)Give a structure for: allyl alcohol
Name _________________________________________________ Third Drill Test (Sample B)
Organic Chemistry 2210 DR
Answer All Questions
1) Name:
4) Give a structure for:
1,3-di-tert-butylcyclohexene
2) Name:
5) Give a structure for: vinyl chloride
Br
3) Name:
F
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6) Name BrCH2 CH2 CHBr2
11)Give a structure for: 2,3-dimethylpentane
7) Name:
12)Give a structure for:
2,2-dimethylbicyclo[3.2.1]octane
8) Name: BrCHCH2 CHCH 3
|
|
CH2
CHOH
|
|
CH2 I CH2 Cl
13)Give a structure for:
4-tert-butyl-4-ethylcyclohexanol
9) Name:
14)Give a structure for:
3,5-dichloro-4-iodononane
CH3 CHCH 2
|
CH3
10)Name:
15) Give a structure for: sec-butyl alcohol
CH3 CHCH 3
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